


The Twink Hipster & The Grumpy Businessman

by Master Thief (lucid_lies)



Category: Teen Wolf (TV)
Genre: Alive Cora Hale, Alive Laura Hale, Alive Vernon Boyd & Erica Reyes, Alternate Universe, Awkward Flirting, Awkwardness, Businessman Derek, Dating, Grumpy Derek, M/M, Matchmaker Stiles, Matchmaking, Misunderstandings, Oblivious Stiles, Romance, Romantic Comedy, Sarcastic Stiles, Sassy Stiles, Sexual Tension, Slow Build Derek Hale/Stiles Stilinski, Sourwolf Derek Hale, Use Your Words, Where Derek totally thinks Stiles is a hooker
Language: English
Status: In-Progress
Published: 2015-01-22
Updated: 2015-01-22
Packaged: 2018-03-08 15:00:24
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,345
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3213425
Author URL: https://archiveofourown.org/users/lucid_lies/pseuds/Master%20Thief
Summary: <blockquote class="userstuff">
              <p>[AU, Rom-Com]</p>
<p>Wherein Derek confuses Stiles - the matchmaker Laura hired, cause Derek totally needs to get laid - with a twink prostitute. After many bad dates and awkward flirting, he falls in love.</p>
            </blockquote>





	The Twink Hipster & The Grumpy Businessman

**Author's Note:**

> This originally had a nice, serious title in French but my friend convinced me to change it. She hopes you get a laugh out of it. It's going to be a total rom-com, I just know it. What can I say? I wanted matchmaking twinky!hipster!Stiles and grumpy!workaholic!Derek. And, uh...if you don't know what a twink is, I suggest using Google (which I got the divider from, fyi). Broadening the mind and all that rot. Also, I envision Stiles looking like Dylan did in The Internship but you can imagine him however you please. I hope you enjoy the result.

“Laura, what the hell do you want?”

Derek Hale, CEO of Hale Industries, a relatively wealthy privately funded company with assets in bio-medical research, sinks back into his office chair with an exasperated sigh. He has a meeting in less than ten minutes with an ambassador from Japan and here he is, stuck on the phone with his older sister because she’s up to no good.

“I am so offended, Der-Bear,” she says, voice crackling over the speaker, sounding decidedly unapologetic and smug. “Here I am, checking up on my baby brother like a good big sister, and he’s questioning my motives.”

He raises a wry eyebrow, lips twitching in amusement as he fires back a response. “Your words wound me, Laura. Truly. I don’t know how I can possibly live with myself.”

A soft gasp sounds and when she beings to talk again, Derek can hear the smothered amusement in her voice.

“How terribly cruel you can be, Little Brother. And are you raising your eyebrow at me again?”

“No.”

A beat of silence stretches between them before Laura breaks it with a snort, her laughter ringing in his ears.

“Oh, you totally did, didn’t you?”

“No, I didn’t.”

“Oh, yes you did. I know you did.”

He scowls at the phone, glancing down at the watch fixed to his wrist. The meeting starts in six minutes. He has to end this, and soon. He can’t keep a foreign visitor waiting on his behalf just because his older sister decided she wants to make his life hell today.

“Laura?”

“Yes, Der?”

“Shut up.”

He hears her shuffling something over the phone. She’s probably slacking off in her office which just so happens to be two floors down from his own.

“You’re always so grumpy,” she says. “You need to get laid.”

Derek groans, fingers pinching the bridge of his nose. This is the same old argument between them. Laura makes it a point of calling him at least twice a week to remind him of his rather lacking love life.

“Laura, what do you want? I’ve got to get to a meeting.”

She huffs, rapping her nails against the side of her phone, the sound unpleasantly loud in his ear.

“You are such a workaholic, it’s not healthy.”

“Yeah, well some of us need to actually work instead of batting our eyelashes.”

“Hey, you’ve got pretty enough eyelashes yourself, Der. You should try batting them sometime. At someone. Y’know, to have sex.”

Derek rolls his eyes at Laura’s persistence, you’d think an older sister wouldn’t be so interested and invested in her younger brother’s sex life but that’s Laura, ripping through boundaries like they're tissue paper. He gives a curt nod to his secretary when she props the door open to tell him the ambassador is ready for him.

“ - I mean, just put yourself out there, Der. You’ve got a great ass, I’m sure loads of guys - “

“If you’re finished, I’ve got a meeting to attend,” he interrupts her rant, pushing himself out of the plush chair and attempting to straighten the creases out of his suit with one hand.

“Wait, Der, before you go- “

“Laura, I’m hanging up now.”

“No, wait! You need to know, I set something up and around three o’clock today someone is - “

“Bye, talk to you later.”

“Derek- !”

Pressing the end call button has never felt so satisfying.

Pocketing his phone, Derek smooths down his suit and makes his way to the conference room. It’s time to win over a new partner and he never loses.

Derek sags against the cushion, head tipping back against the headrest. Rolling his shoulders, he lets out a groan, muscles bunching and releasing. It’s been a long day and it isn’t even over yet. He’s still got a good three hours left before he can leave. Admittedly it’s just some last minute paperwork that he has to look over and approve but that’s not the point.

After his usually disastrous phone call with Laura, he sat down in front of his board members and the representatives of an affluent Japanese bio-medical research team, charming his way into their back pockets. By the end of the meeting, he’d been invited to five different dinner parties and even a few arranged marriage proposals. All that doesn't matter to him though because he got what he wanted. The entire reason for the meeting was to buy out their extensive research on skin grafting. And like always, Derek never fails.

No matter how good he is at playing the game, that doesn’t make it any less exhausting. Preferably, Derek likes to spend his time with himself. People are just so exhausting. Someone always wants something. After fulfilling peoples expectations for nearly half his lifetime, he’s sick of it. So, solitude. He knows it drives Laura up the wall - she’s always saying he needs to get out and have a little fun - but it’s honestly the best solution he’s found to date. That and throwing himself head first into his work. Can’t be bothered with socializing when you’re busy, now can you?

His fingers pluck at his tie, loosening the knot as he lounges in his office. The stack of crisp white papers sit on the left side of his desk (he’s got issues with placement, papers always go on the left) waiting to be rubber stamped by him. Most of the employees have left for the day, the only ones left behind are the higher ups, Derek included. He might own this company and be able to leave whenever the hell he wants to, but he feels it's unfair to everyone if they’re stuck here doing his work while he’s off gallivanting around town. So he stays until the office closes for the night. It’s the least he can do.

He’s just closed his eyes for a cat nap when a hesitant knock disrupts the quiet of his otherwise empty office. Cracking open an eye, he calls out for the person to come in, it’s open. It’s probably just Janice, his secretary, wishing him a good night.

_Oh._

“You’re definitely not Janice…”

There’s a young man - boy really - standing in the threshold, an uneasy smile stretching across his wide mouth. He’s got a wreath of dark messy hair that looks like he keeps running his hands through it, and thick framed glasses are perched on the bridge of his nose. He’s tall but lanky and he’s wearing a god awful button up, tight black jeans and converse. Derek can’t help but notice there’s a security badge hanging from his neck.

He gives an awkward cough and a half-hearted wave.

“Hey, uh, Derek Hale, right?” the boy asks, voice surprisingly deep and smooth.

Derek feels like an idiot but he can’t help just staring at the bizarre young man that popped up out of no where, repeatedly blinking as if that would make the person in front of him disappear.

He shuffles his feet, eyes bouncing between the sleek office and Derek’s slack face. He scratches at his jaw absently before clearing his throat.

“I don’t know if - well, Laura Hale…” He stops, scuffing a shoe across the grey carpet. He makes a gesture with his hand like that explains why he’s in Derek’s office. “She, y’know, asked for my services.”

Derek’s eyebrows steadily climb towards his hairline. Did Laura really do what Derek thinks she did? There’s no way. She wouldn’t - but then again, she would. This has his sister written all over it. Rubbing at his temple where he feels a migraine coming on, Derek fishes his phone out of his pocket, hitting speed dial.

“Hey, you okay buddy?” The boy’s frowning, shuffling forward a few steps. A quick glare from Derek stops any and all movement. He goes back to awkwardly looking around, fingernails plucking at a frayed string hanging off his sleeve. “Okay, we’re cool, we’re cool. I’ll just, yeah…”

Laura answers after the third ring.

“Hello?”

“Laura,“ Derek pauses, eyeing the young boy shrewdly, “Did you seriously hire a twink prostitute for me?”

 


End file.
